Pesticidally active heterocyclic derivatives with sulphur containing substituents

Patent metadata

Field	Value
Publication number	US-9775353-B2
Application number	US-201515323983-A
Country	US
Kind code	B2
Filing date	Jul 2, 2015
Priority date	Jul 8, 2014
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

Compounds of formula (I), wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.

First claim

The invention claimed is:

1. A compound of formula I,

wherein
A represents CH or N;
each R is, independently from each other, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, halogen, cyano, cyanoC 1 -C 4 alkyl, tri(C 1 -C 4 alkyl)silyl, C 1 -C 4 alkoxyC 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanylC 1 -C 4 alkoxy or nitro;
or each R is, independently from each other, phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl and cyano;
n is 0, 1, 2, 3, 4 or 5;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl mono-, di- or trisubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
or R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;
R 2 is halogen, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano;
or R 2 is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl) or —C(O)C 1 -C 4 haloalkyl;
or R 2 is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; and
X 1 is O, S or NR 3 , wherein R 3 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

2. A compound of formula I according to claim 1 , represented by the compounds of formula I-1

wherein
R, R 2 and n are as defined under formula I in claim 1 ;
Xa 1 is S, SO or SO 2 ; and
Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. A compound of formula I-1 according to claim 2 , wherein
n is 1 and R is halogen, cyano or C 1 -C 4 haloalkyl.

4. A compound of formula I according to claim 1 , represented by the compounds of formula I-2

wherein
R, R 2 and n are as defined under formula I in claim 1 ;
Xa 2 is S, SO or SO 2 ; and
Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

5. A compound of formula I-2 according to claim 4 , wherein
n is 1 and R is halogen, cyano or C 1 -C 4 haloalkyl.

6. A compound of formula I according to claim 1 , represented by the compounds of formula Ia

wherein
X 2 is SO 2 ;
X 3 is N—C 1 -C 4 alkyl;
R 4 is C 1 -C 4 alkyl;
R 5 is halogen, C 1 -C 4 haloalkyl, cyano or C 1 -C 4 alkoxy;
n is 1, 2 or 3; and
R 6 is C 1 -C 4 haloalkyl.

7. A compound of formula I according to claim 1 , represented by the compounds of formula Ib

wherein
A is N or CH;
X 2 is S or SO 2 ;
X 3 is N—C 1 -C 4 alkyl;
R 7 is C 1 -C 4 alkyl;
R 8 is halogen, cyano, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;
n is 0, 1, 2 or 3; and
R 9 is C 1 -C 4 haloalkyl.

8. A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.

Assignees

• Syngenta Participations Ag

Inventors

• Stoller Andre
• Jeanguenat Andre
• Edmunds Andrew
• Jung Pierre Joseph Marcel
• Emery Daniel
• Muehlebach Michel
• Renold Peter

Classifications

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• C07F5/025

  Boronic and borinic acid compounds · CPC title

• A01N55/08

  containing boron · CPC title

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title